Tag: M.W=100-200

13531-48-1, name is Methyl 3-cyanobenzoate, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C9H7NO2

General procedure: To a solution of cyanide (8.0 mmol) in 20 mL ethanol was added hydroxylamine (solution 50% in water) (4.0 mL) at room temperature. Thereaction mixture was stirred atreflux for 3 to 4 hours until the nitriles were completed converted(monitored by TLC). The mixture solution was evaporated and extracted withdichloromethane (10 mL¡Á3). The combined organic layers were washed with brine(10 mL), dried over anhydrous Na2SO4, filtered andconcentrated to give the crude product, which was further purified by columnchromatography to afford compounds 4and 8.

The synthetic route of 13531-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Mei; Li, Shan; Ai, Jing; Sheng, Rong; Hu, Yongzhou; Hu, Youhong; Geng, Meiyu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5679 – 5684;,
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Electric Literature of 453565-55-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 453565-55-4, name is 5-Fluoroisophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

5-Morpholinoisophthalonitrile.; A mixture of 5-fluoroisophthalonitrile (1.00 g, 6.84 mmol, 1.0 eq.), morpholine (1192 mul, 13.69 mmol, 2.0 eq.), and DMSO (2.0 ml) was stirred overnight at 500C. The mixture was diluted with 2% aq. HCl (30 ml), the solid was separated by filtration, washed with 2% aq. HCl, water, and dried in HV to give pure target product (white solid, 1.35 g, 92% yield, 99% pure by LCMS – no mass observed). 1H-NMR (DMSO-d6) delta (ppm) 7.69 (s, 3H), 3.71 (m, 4H), 3.28 (m, 4H).

The chemical industry reduces the impact on the environment during synthesis 5-Fluoroisophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KEMIA, INC.; WO2008/21388; (2008); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 34916-10-4 as follows. Formula: C7H9NO

To a stirred solution of R-06i-3 (4.00 g, 32.48 mmol) and KHMDS (1 .0 M, 42.87 mL, 42.87 mmol) in THF (200 mL) under N2at -78 C was added PhNTf2(14.85 g, 41 .57 mmol) and the reaction mixture was stirred at 20 C for 8 hours. Then, the mixture was cooled to 20 C and concentrated in reduced pressure at 40 C. The residue was poured into water and extracted with ethyl acetate. The combined organic phase was washed with brine, dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate = 50/1 to 1 :1 ) to give R-06i- 4 (3.00 g, 36%) as a colorless oil. ESI-MS (M+1 ): 256.1 calc. for C8H8F3N03S: 255.0.

According to the analysis of related databases, 34916-10-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUNDACION PARA LA INVESTIGACION MEDICA APLICADA; AGUIRRE ENA, Xabier; OYARZABAL SANTAMARINA, Julen; PROSPER CARDOSO, Felipe; RABAL GRACIA, Maria Obdulia; SAN JOSE ENERIZ, Edurne; SANCHEZ ARIAS, Juan Antonio; VILAS ZORNOZA, Amaia; (96 pag.)WO2018/229139; (2018); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C12H6N2O

7.1. Under argon (Ar) protection, add 0.43 mmol (486 mg) of intermediate M1 to a 100 mL three-necked bottle.1.73 mmol (336 mg) of 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile and 30 mL of chloroform.7.2. Add 1 mL of pyridine to the flask and react at 65 C for 24 hours.The reaction was stopped, the solvent was spun off, the mixture was taken up in methanol and filtered to give a crude product.7.3. The crude product is separated and purified by column chromatography. The eluent is a mixed solution of dichloromethane and petroleum ether in a volume ratio of 1..1.A black solid of 450 mg was obtained in a yield: 70%. That is, the small molecule LS1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1080-74-6.

Reference:
Patent; Xiangtan University; Shen Ping; Liang Jingtang; Yin Pan; Zheng Tao; Zeng Xiaoying; (32 pag.)CN110283184; (2019); A;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Product Details of 10406-25-4

4-(Aminomethyl)benzonitrile (25.09 g, 0.149 mol) and L-cysteine (18.1 g, 0.149 mol) were suspended in 500 mL MeOH and pH 6.4 buffer solutions (1 : 1) and stirred for 3 days at RT. Triethylamine (30 mL) was added to the mixture and Boc20 (68 g, 0.31mol) was added to this mixture and stirred for 2 h. The solvents were removed and filtered to yield white solid (R)-2-(4-((?ri-butoxycarbonylamino)methyl)phenyl)-4,5-dihydrothiazole-4- carboxylic acid (38.4 g, 76.8%). Compound 67a was obtained from this acid following the same method as used for 38d. Yield: 84.4 %. 1H NMR (500 MHz, CDC13) delta 7.75 – 7.77 (d, 2 H, J = 7.5 Hz), 7.27 – 7.26 (d, 2 H, J = 7.5 Hz), 7.23 (s, 1 H), 5.62 (br, 1 H), 4.87 (br, 1 H), 4.30 (br, 2 H), 3.86 (s, 3 H), 3.78 (t, J = 10.0 Hz, 1 H), 3.48 – 3.4 (m, 1 H), 3.25 (s, 3 H), 1.42 (s, 9 H). MS (ESI) m/z 402.1(M + Na)+, 378.0 (M – H)-.

The synthetic route of 10406-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; DALTON, James, T.; MILLER, Duane, D.; AHN, Sunjoo; CHEN, Jianjun; DUKE, Charles; LI, Chien-ming; LI, Wei; LU, Yan; WANG, Zhao; WO2011/109059; (2011); A1;,
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Reference of 21803-75-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 4-amino-3-chlorobenzonitrile (52 mg, 0.34 mmol), CS2CO3 (130 mg, 0.4 mmol) were added to tert-butyl 5-chloro-3-formyl-6-methylpyrazolo[l,5-a]pyrimidin-7- yl(cyclopropyl)carbamate (100 mg, 0.29 mmol) dissolved in 1,4-dioxane (1.1 mL). Racemic BINAP (11 mg, 0.017 mmol) and palladium(II) acetate (8 mg, 0.011 mmol) were then added. The mixture was sealed and irradiated at 110 C for 60 min in the microwave. Et20 (3 mL) was added and the solution was filtered. The filtrate was concentrated in vacuo. The crude residue was dissolved in dichloromethane (1.5 mL) and trifluoroacetic acid (1.5 mL). After stirring at room temperature for 1 hour, the solution was concentrated under a stream of air. The crude material was purified by silica gel chromatography (3% acetone/dichloromethane) to yield the product, 3-chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[l,5- a]pyrimidin-5-ylamino)benzonitrile (34 mg, 33% yield). LCMS (M+l=367)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Amino-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYLENE PHARMACEUTICALS INC.; HADDACH, Mustapha; RYCKMAN, David; RAFFAELE, Nicholas; WO2011/31979; (2011); A1;,
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Application of 1080-74-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows.

Add 4,4-((([2,1,3] -benzoseladiazole-4,7-substituent bis (4-dodecylthiophene-5,2-substituent)) di (4, 1-phenylene)) bis (aniline) dibenzaldehyde (737mg, 0.599mmol) and 3- (dicyanomethylene) indone (348.7mg, 1.797mol) were added to a 100ml round bottom flask,Add 80 ml of trichloromethane and 10 ml of pyridine. After reacting at room temperature for 6 hours, pour the reaction solution into ethanol to precipitate a large amount of blue-black solids at this time, filter, dissolve the solid with dichloromethane, and purify by column chromatography. Methane: petroleum ether = 3: 1 was used as an eluent to separate the crude product, and then recrystallized from dichloromethane and ethanol to obtain a blue-black powdery solid (345 mg, 36.5%). The blue-black powdery solid is IND-TPA-Th-BSe, and its NMR experimental data is as follows:

The chemical industry reduces the impact on the environment during synthesis 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiangxi Normal University; Liang Aihui; Zhou Wenjing; Zhang Jiayu; Hu Sifan; Xie Qi; Liu Zhiqian; (13 pag.)CN110229148; (2019); A;,
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Related Products of 73629-43-3,Some common heterocyclic compound, 73629-43-3, name is 2,3-Diaminobenzonitrile, molecular formula is C7H7N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

2,3-Diaminobenzonitrile (80 mg; may be prepared as described in intermediate 164) was taken up in ethanol (10 ml). Ethyl 3-bromo-2-oxopropanoate (0.076 ml; Aldrich) was added and left to stir at room temperature overnight. The reaction mixture was filtered, leaving a light orange solid as the residue (15mg). The filtrate was concentrated under vacuum. It was then diluted with DCM and purified, along with the residue, using silica chromatography (10 – 70% EtOAc / isohexane) to give the title compound (70 mg) as an orange solid, m/z [M+H]+: 264.0 / 266.0. Retention time 0.72 min (LC/MS method 3).

The synthetic route of 73629-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile

[00308] A mixture of (2,2-difluoro-l ,3-benzodioxol-5-yl)-acetonitrile (1.0 eq), 50 wt % aqueous KOH (5.0 eq) 1 -bromo-2-chloroethane (1.5 eq), and Oct4NBr (0.02 eq) was heated at 70 C for 1 h. The reaction mixture was cooled, then worked up with MTBE and water. The organic phase was washed with water and brine. The solvent was removed to afford (2,2-difluoro-l ,3- benzodioxol-5-yl)-cyclopropanecarbonitrile.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SWINNEY, Kelly, Ann; HURTER, Patricia, Nell; NADIG, David, E.; SMITH, David; THOMAS, Vance, Hayden; WARMAN, Martin, Paul; WO2015/73231; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3939-09-1, name is 2,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3F2N

A mixture of 2, 4-Difluoro-benzonitrile (1.39 g, 10 mmol) , 3- amino-propane-1, 2-diol (0.911 g, 10 mmol) , and ethyl- diisopropyl-amine (1.74 mL) in DMSO (10 itiL) was microwaved at 200 0C for 7 min. Then the reaction mixture was poured into a saturated NH4Cl aq. solution (100 mL) , extracted with EtOAc (3×100 mL) , dried over Na2SCu, filtered, concentrated. The crude mixture was purified by flash silica gel chromatography (EtOAc-Hexane 1:1) to give 2- (2, 3-Dihydroxy-propylamino) -4- fluoro-benzonitrile (0.87 g, 41.4% yield). LCMS (m/z) : M+H = 211.To a mixture of 6, 6-Dimethyl-3-trifluoromethyl-l, 5, 6, 7- tetrahydro-indazol-4-one (0.961 g, 4.14 mmol, 1 eq) and NaH (99 ?ig, 4.14 mmol, 1 eq) in dimethyl acetamide (20 mL) was added slowly 2- (2, 3-Dihydroxy-propylamino) -4-fluoro- benzonitrile (0.87 g, 4.14 mmol, 1 eq) . Then the reaction mixture was stirred at 150 C overnight, cooled, poured into saturated NH4Cl aq. solution (100 mL) , extracted by EtOAc(3×150 mL) , dried over Na2SO4, filtered, concentrated. The crude product was purified by flash silica gel chromatography, eluted by EtOAc to give 2- (2, 3-Dihydroxy-propylamino) -4- (6, 6- dimethyl-4-oxo-3-trifluoromethyl-4 , 5,6, 7-tetrahydro-indazol-l- yl)-benzonitrile (1.7g, 97% yield). LCMS (m/z): M+H = 423. 2- (2, 3-Dihydroxy-propylamino) -4- (6, 6-dimethyl-4-oxo-3- trifluoromethyl-4, 5, 6, 7-tetrahydro-indazol-l-yl) -benzonitrile (1.7 g, 4 mmol, 1 eq) , NaOH (806 mg, 20 mmol, 5 eq) , and H2O2 EPO (3 iriL) were dissolved in EtOH-water (4:1) (40 itiL) . The mixture was microwaved at 120 C for 15 min, then concentrated to dryness, and purified by flash chromatography, eluted by 10% MeOH in EtOAc to give pure 2- (2, 3-Dihydroxy-propylamino) – 4- (6, beta-dimethyl-4-oxo-3-trifluoromethyl-4, 5, 6, 7-tetrahydro- indazol-1-y l)-benzamide (0.52 g, 29% yield). LCMS (m/z) : M+H = 441.

The synthetic route of 3939-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (2006); A1;,
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